In this contribution, we present the synthesis and self‐assembly of alkylated thioethers with interesting photophysical properties. To this end, the emission, absorption and excitation spectra in organic solvents and as aggregates in water were measured as well as the corresponding photoluminescence quantum yields and lifetimes. The aggregates in aqueous media were visualized and measured using transmission electron microscopy. Besides that, crystal structures of selected compounds allowed a detailed discussion of the structure–property relationship. Furthermore, the mesomorphic behavior was investigated using polarized optical microscopy (POM) as well as differential scanning calorimetry (DSC).
In this contribution we report on the synthesis, characterization and application of water-soluble zinc(II) phthalocyanines, which are decorated with four or eight umbelliferone moieties for photodynamic therapy (PDT). These compounds are linked peripherally to zinc(II) phthalocyanine by a triethylene glycol linker attached to pyridines, leading to cationic pyridinium units, able to increase the water solubility of the system. Beside their photophysical properties they were analyzed concerning their cellular distribution in human hepatocyte carcinoma (HepG2) cells as well as their phototoxicity towards HepG2 cells, Gram-positive (S. aureus strain 3150/12 and B. subtilis strain DB104) and Gram-negative bacteria (E. coli strain UTI89 and E. coli strain Nissle 1917). At low light doses and concentrations, they exhibit superb antimicrobial activity against Gram-positive bacteria as well as anti-tumor activity against HepG2. They are even capable to inactivate Gram-negative bacteria, whereas the dark toxicity remains low. These unique water-soluble compounds can be regarded as all-in-one type photosensitizers with broad applications ranges in the future.
In this work we present a full study on the influence of substitution patterns in aromatic thioether-based luminogens with aggregation induced emission properties. To this end nine different compounds, either with nitrile groups in ortho, meta or para positions as well as phenol groups in different positions were synthesized and investigated concerning their photophysical properties. Besides that, eight compounds were obtained as single crystals for X-ray analysis to get a deeper understanding on the packing parameters, secondary interac-tions as well their influence on the properties of these compounds. Time dependent density functional theory calculations helped to understand the distribution of the frontier orbitals. Moreover, these nanostructures were analysed concerning their applicability as cellular markers. We could thus show that indeed subtle differences in shape and substitution pattern dramatically influence the photophysical properties as well as cellular uptake of the compounds.[a] J.
A novel class of cationic amphiphiles based on estrone with aggregation-induced emission (AIE) properties is described which is able to transfect different cell lines. The AIE-effect is used to track the transfection process.
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